This chapter focuses on the concepts of anonymity and transparency to reach a level of conceptual clarity that can ground the following investigations. It addresses the role of encryption and the multifold understandings of anonymity and transparency in the crypto-asset sphere and related transactions. Its disambiguation efforts target the crossroads between different conceptual levels pertaining to the cyberspace, crypto-asset ecosystems, financial transactions. It explores the traits featured by anonymity and transparency within an AML/CFT context and provides an analysis of several features of crypto-asset anonymity. Meanwhile, the chapter investigates the twofold notion of transparency, torn by the constitutive difference between the concepts of ledger transparency and financial transparency. Accordingly, it reframes the alleged paradox of public blockchains being both anonymous and transparent. Finally, it addresses enhanced disintermediation and its impact on accountability.